1-(5-Hydroxy-1-phenyl-3-trifluoromethyl-1H-pyrazol-1-yl)ethanone.

The crystal structure of the title compound, C(12)H(9)F(3)N(2)O(2), contains two independent mol-ecules in the asymmetric unit. The mol-ecules are chemically identical but exhibit a significant difference in the dihedral angles between the mean planes of the phenyl and pyrazole rings, with values of of 11.62 (13) and 18.17 (11)°. Moreover, the trifluoro-methyl group in one of the mol-ecules shows rotational disorder of the F atoms, with site occupancy factors of 0.929 (6) and 0.071 (6). The hydroxyl group in each of the mol-ecules shows a strong intra-molecular hydrogen bond with the carbonyl O atom, forming a six-membered ring and forcing the formyl group and pyrazole ring to be coplanarshowing C-C-C-O torsion angles of ?0.3(5)o and 0.°. Weak inter-molecular C-H⋯O and C-H⋯F inter-actions contribute to the stabilization of the crystal packing.

Related literature

For the pharmaceutical activity of pyrazole derivatives, see: Belmar et al. (2001 ▶). For related structures, see: Gallardo et al. (2009 ▶); Belmar et al. (2006a ▶,b ▶); Pérez et al. (2005 ▶). For the melting point, see: Bieringer & Holzer (2006 ▶).

Experimental

Crystal data

C12H9F3N2O2

M = 270.21

Triclinic,

a = 7.4779 (19) Å

b = 11.9390 (18) Å

c = 13.8587 (14) Å

α = 78.591 (11)°

β = 80.090 (17)°

γ = 78.791 (18)°

V = 1178.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.40 × 0.33 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4766 measured reflections

4567 independent reflections

2268 reflections with I > 2σ(I)

R int = 0.025

3 standard reflections every 200 reflections

intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.165

S = 1.04

4567 reflections

373 parameters

81 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1996 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051745/pv2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051745/pv2233Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H9F3N2O2	Z = 4
Mr = 270.21	F(000) = 552
Triclinic, P1	Dx = 1.523 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.4779 (19) Å	Cell parameters from 25 reflections
b = 11.9390 (18) Å	θ = 5.4–18.6°
c = 13.8587 (14) Å	µ = 0.14 mm−1
α = 78.591 (11)°	T = 293 K
β = 80.090 (17)°	Prismatic, yellow
γ = 78.791 (18)°	0.40 × 0.33 × 0.13 mm
V = 1178.2 (4) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.025
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.5°
graphite	h = −9→9
ω/2θ scans	k = −14→14
4766 measured reflections	l = −17→0
4567 independent reflections	3 standard reflections every 200 reflections
2268 reflections with I > 2σ(I)	intensity decay: 1%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.4943P] where P = (Fo2 + 2Fc2)/3
4567 reflections	(Δ/σ)max = 0.001
373 parameters	Δρmax = 0.20 e Å−3
81 restraints	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.4429 (3)	0.5800 (2)	0.73982 (18)	0.0517 (7)
N2	0.4653 (4)	0.6690 (2)	0.66084 (18)	0.0585 (7)
C3	0.4755 (5)	0.7585 (3)	0.7002 (2)	0.0557 (8)
C4	0.4619 (4)	0.7333 (3)	0.8049 (2)	0.0524 (8)
C5	0.4399 (4)	0.6175 (3)	0.8262 (2)	0.0536 (8)
O5	0.4173 (3)	0.55236 (19)	0.91394 (16)	0.0695 (7)
H5	0.4804	0.6027	0.9610	0.083*
C6	0.4214 (4)	0.4699 (3)	0.7213 (2)	0.0508 (8)
C7	0.4301 (5)	0.3738 (3)	0.7950 (3)	0.0668 (10)
H7	0.4494	0.3792	0.8583	0.080*
C8	0.4099 (5)	0.2695 (3)	0.7735 (3)	0.0749 (11)
H8	0.4140	0.2046	0.8233	0.090*
C9	0.3840 (5)	0.2594 (3)	0.6807 (3)	0.0738 (11)
H9	0.3725	0.1881	0.6670	0.089*
C10	0.3752 (5)	0.3559 (3)	0.6079 (3)	0.0718 (10)
H10	0.3567	0.3499	0.5446	0.086*
C11	0.3934 (5)	0.4620 (3)	0.6275 (2)	0.0633 (9)
H11	0.3869	0.5271	0.5779	0.076*
C12	0.4960 (7)	0.8687 (3)	0.6304 (3)	0.0751 (11)
F1	0.5010 (8)	0.8597 (3)	0.5363 (2)	0.1229 (17)	0.929 (6)
F1''	0.362 (5)	0.899 (4)	0.585 (3)	0.119 (13)	0.071 (6)
F2	0.3541 (5)	0.9518 (2)	0.6488 (3)	0.1112 (14)	0.929 (6)
F2''	0.508 (7)	0.955 (3)	0.667 (3)	0.106 (11)	0.071 (6)
F3	0.6442 (6)	0.9097 (3)	0.6361 (3)	0.1119 (14)	0.929 (6)
F3''	0.637 (6)	0.850 (3)	0.573 (3)	0.096 (12)	0.071 (6)
C13	0.4653 (5)	0.7924 (3)	0.8855 (3)	0.0643 (9)
O13	0.4473 (4)	0.7366 (2)	0.97198 (18)	0.0839 (8)
C14	0.4909 (6)	0.9153 (3)	0.8704 (3)	0.0849 (12)
H14A	0.4708	0.9407	0.9335	0.127*
H14B	0.4046	0.9625	0.8290	0.127*
H14C	0.6140	0.9221	0.8388	0.127*
N1'	0.9141 (4)	0.4419 (2)	0.7688 (2)	0.0561 (7)
N2'	0.9250 (4)	0.3460 (2)	0.8425 (2)	0.0612 (7)
C3'	0.9172 (4)	0.2592 (3)	0.7996 (3)	0.0587 (9)
C4'	0.9010 (4)	0.2929 (3)	0.6972 (2)	0.0578 (9)
C5'	0.8996 (4)	0.4117 (3)	0.6816 (2)	0.0569 (8)
O5'	0.8858 (3)	0.4856 (2)	0.59906 (17)	0.0747 (7)
H5'	0.8542	0.4376	0.5487	0.090*
C6'	0.9283 (4)	0.5517 (3)	0.7911 (2)	0.0536 (8)
C7'	0.9738 (5)	0.6410 (3)	0.7169 (3)	0.0655 (9)
H7'	0.9917	0.6317	0.6506	0.079*
C8'	0.9925 (5)	0.7435 (3)	0.7409 (3)	0.0737 (11)
H8'	1.0230	0.8038	0.6908	0.088*
C9'	0.9668 (5)	0.7580 (3)	0.8383 (3)	0.0778 (11)
H9'	0.9813	0.8276	0.8542	0.093*
C10'	0.9198 (5)	0.6702 (3)	0.9119 (3)	0.0768 (11)
H10'	0.9013	0.6805	0.9779	0.092*
C11'	0.8993 (5)	0.5662 (3)	0.8896 (3)	0.0652 (9)
H11'	0.8666	0.5067	0.9399	0.078*
C12'	0.9344 (6)	0.1406 (3)	0.8617 (3)	0.0736 (10)
F1'	1.0741 (4)	0.06809 (19)	0.8220 (2)	0.1054 (8)
F2'	0.9629 (4)	0.14090 (19)	0.95283 (18)	0.1084 (9)
F3'	0.7860 (3)	0.09262 (18)	0.86974 (18)	0.0964 (8)
C13'	0.8886 (5)	0.2391 (3)	0.6145 (3)	0.0726 (10)
O13'	0.8789 (4)	0.3019 (3)	0.5317 (2)	0.0953 (9)
C14'	0.8891 (7)	0.1121 (3)	0.6241 (3)	0.0989 (14)
H14D	0.8621	0.0961	0.5635	0.148*
H14E	0.7975	0.0886	0.6780	0.148*
H14F	1.0081	0.0701	0.6371	0.148*

	U11	U22	U33	U12	U13	U23
N1	0.0614 (17)	0.0456 (15)	0.0463 (16)	−0.0126 (12)	−0.0084 (13)	0.0007 (12)
N2	0.077 (2)	0.0473 (16)	0.0473 (16)	−0.0152 (13)	−0.0068 (13)	0.0045 (13)
C3	0.068 (2)	0.0430 (18)	0.054 (2)	−0.0103 (16)	−0.0102 (17)	−0.0010 (16)
C4	0.055 (2)	0.0486 (18)	0.053 (2)	−0.0092 (15)	−0.0099 (15)	−0.0037 (15)
C5	0.055 (2)	0.056 (2)	0.0487 (19)	−0.0117 (16)	−0.0067 (15)	−0.0035 (16)
O5	0.0961 (19)	0.0660 (15)	0.0460 (13)	−0.0251 (13)	−0.0112 (12)	0.0044 (11)
C6	0.050 (2)	0.0445 (18)	0.056 (2)	−0.0085 (14)	−0.0029 (15)	−0.0060 (15)
C7	0.077 (3)	0.055 (2)	0.066 (2)	−0.0159 (18)	−0.0112 (19)	0.0008 (18)
C8	0.084 (3)	0.050 (2)	0.086 (3)	−0.0157 (19)	−0.011 (2)	0.002 (2)
C9	0.073 (3)	0.052 (2)	0.098 (3)	−0.0164 (18)	−0.002 (2)	−0.019 (2)
C10	0.086 (3)	0.064 (2)	0.070 (2)	−0.022 (2)	−0.006 (2)	−0.018 (2)
C11	0.079 (3)	0.054 (2)	0.057 (2)	−0.0170 (18)	−0.0042 (18)	−0.0073 (17)
C12	0.107 (4)	0.053 (2)	0.064 (3)	−0.017 (2)	−0.013 (3)	−0.002 (2)
F1	0.244 (5)	0.0707 (18)	0.0569 (19)	−0.053 (2)	−0.025 (2)	0.0120 (14)
F1''	0.18 (2)	0.10 (2)	0.07 (2)	−0.04 (2)	−0.05 (2)	0.033 (19)
F2	0.137 (3)	0.0565 (17)	0.121 (3)	0.0069 (18)	−0.022 (2)	0.0097 (16)
F2''	0.15 (3)	0.059 (18)	0.12 (2)	−0.049 (19)	−0.05 (2)	0.007 (16)
F3	0.118 (3)	0.087 (2)	0.135 (3)	−0.059 (2)	−0.030 (2)	0.023 (2)
F3''	0.14 (2)	0.060 (18)	0.08 (2)	−0.040 (17)	−0.042 (19)	0.052 (16)
C13	0.064 (2)	0.062 (2)	0.069 (2)	−0.0067 (17)	−0.0114 (18)	−0.0165 (19)
O13	0.118 (2)	0.0789 (18)	0.0542 (16)	−0.0138 (15)	−0.0083 (15)	−0.0153 (14)
C14	0.107 (3)	0.064 (2)	0.093 (3)	−0.014 (2)	−0.018 (2)	−0.032 (2)
N1'	0.0623 (18)	0.0467 (16)	0.0565 (17)	−0.0101 (13)	−0.0075 (14)	−0.0023 (13)
N2'	0.0710 (19)	0.0489 (17)	0.0611 (18)	−0.0104 (14)	−0.0097 (14)	−0.0021 (14)
C3'	0.057 (2)	0.049 (2)	0.070 (2)	−0.0112 (16)	−0.0084 (17)	−0.0059 (17)
C4'	0.057 (2)	0.057 (2)	0.061 (2)	−0.0148 (16)	−0.0053 (17)	−0.0095 (17)
C5'	0.053 (2)	0.061 (2)	0.054 (2)	−0.0096 (16)	−0.0055 (16)	−0.0046 (17)
O5'	0.0982 (19)	0.0699 (16)	0.0563 (15)	−0.0246 (14)	−0.0168 (13)	0.0045 (13)
C6'	0.0479 (19)	0.0483 (19)	0.062 (2)	−0.0051 (15)	−0.0083 (16)	−0.0067 (16)
C7'	0.070 (2)	0.054 (2)	0.067 (2)	−0.0113 (17)	−0.0032 (18)	−0.0036 (18)
C8'	0.077 (3)	0.050 (2)	0.088 (3)	−0.0139 (18)	−0.008 (2)	0.002 (2)
C9'	0.080 (3)	0.057 (2)	0.102 (3)	−0.0088 (19)	−0.022 (2)	−0.020 (2)
C10'	0.089 (3)	0.065 (3)	0.080 (3)	−0.008 (2)	−0.021 (2)	−0.019 (2)
C11'	0.072 (2)	0.058 (2)	0.064 (2)	−0.0108 (18)	−0.0118 (18)	−0.0035 (18)
C12'	0.086 (3)	0.056 (2)	0.080 (3)	−0.015 (2)	−0.017 (2)	−0.008 (2)
F1'	0.1063 (19)	0.0639 (14)	0.130 (2)	0.0090 (13)	−0.0078 (16)	−0.0090 (14)
F2'	0.175 (3)	0.0663 (14)	0.0878 (18)	−0.0275 (15)	−0.0512 (17)	0.0124 (13)
F3'	0.1083 (19)	0.0687 (14)	0.1132 (18)	−0.0376 (13)	−0.0114 (14)	0.0012 (13)
C13'	0.073 (3)	0.075 (3)	0.075 (3)	−0.024 (2)	−0.006 (2)	−0.016 (2)
O13'	0.131 (3)	0.098 (2)	0.0654 (18)	−0.0395 (18)	−0.0116 (17)	−0.0173 (16)
C14'	0.125 (4)	0.083 (3)	0.104 (3)	−0.031 (3)	−0.018 (3)	−0.036 (3)

N1—C5	1.353 (4)	C14—H14C	0.9600
N1—N2	1.378 (3)	N1'—C5'	1.354 (4)
N1—C6	1.432 (4)	N1'—N2'	1.374 (3)
N2—C3	1.312 (4)	N1'—C6'	1.432 (4)
C3—C4	1.413 (4)	N2'—C3'	1.308 (4)
C3—C12	1.488 (5)	C3'—C4'	1.416 (5)
C4—C5	1.392 (4)	C3'—C12'	1.499 (5)
C4—C13	1.440 (5)	C4'—C5'	1.390 (4)
C5—O5	1.311 (4)	C4'—C13'	1.445 (5)
O5—H5	1.1757	C5'—O5'	1.306 (4)
C6—C11	1.375 (4)	O5'—H5'	1.0662
C6—C7	1.376 (4)	C6'—C7'	1.377 (4)
C7—C8	1.377 (5)	C6'—C11'	1.385 (4)
C7—H7	0.9300	C7'—C8'	1.368 (5)
C8—C9	1.364 (5)	C7'—H7'	0.9300
C8—H8	0.9300	C8'—C9'	1.371 (5)
C9—C10	1.373 (5)	C8'—H8'	0.9300
C9—H9	0.9300	C9'—C10'	1.364 (5)
C10—C11	1.383 (4)	C9'—H9'	0.9300
C10—H10	0.9300	C10'—C11'	1.380 (5)
C11—H11	0.9300	C10'—H10'	0.9300
C12—F3''	1.22 (3)	C11'—H11'	0.9300
C12—F1''	1.24 (3)	C12'—F2'	1.317 (4)
C12—F2''	1.26 (3)	C12'—F3'	1.324 (4)
C12—F3	1.315 (5)	C12'—F1'	1.335 (4)
C12—F1	1.323 (5)	C13'—O13'	1.246 (4)
C12—F2	1.331 (5)	C13'—C14'	1.494 (5)
C13—O13	1.249 (4)	C14'—H14D	0.9600
C13—C14	1.486 (5)	C14'—H14E	0.9600
C14—H14A	0.9600	C14'—H14F	0.9600
C14—H14B	0.9600
C5—N1—N2	109.9 (2)	C13—C14—H14C	109.5
C5—N1—C6	130.8 (3)	H14A—C14—H14C	109.5
N2—N1—C6	119.3 (2)	H14B—C14—H14C	109.5
C3—N2—N1	105.6 (2)	C5'—N1'—N2'	110.4 (3)
N2—C3—C4	112.9 (3)	C5'—N1'—C6'	130.3 (3)
N2—C3—C12	116.8 (3)	N2'—N1'—C6'	119.2 (3)
C4—C3—C12	130.3 (3)	C3'—N2'—N1'	105.4 (3)
C5—C4—C3	102.8 (3)	N2'—C3'—C4'	113.0 (3)
C5—C4—C13	119.1 (3)	N2'—C3'—C12'	117.5 (3)
C3—C4—C13	138.1 (3)	C4'—C3'—C12'	129.4 (3)
O5—C5—N1	123.7 (3)	C5'—C4'—C3'	102.8 (3)
O5—C5—C4	127.5 (3)	C5'—C4'—C13'	119.1 (3)
N1—C5—C4	108.8 (3)	C3'—C4'—C13'	138.1 (3)
C5—O5—H5	100.5	O5'—C5'—N1'	123.6 (3)
C11—C6—C7	120.5 (3)	O5'—C5'—C4'	127.9 (3)
C11—C6—N1	118.4 (3)	N1'—C5'—C4'	108.4 (3)
C7—C6—N1	121.1 (3)	C5'—O5'—H5'	104.8
C6—C7—C8	119.0 (3)	C7'—C6'—C11'	120.1 (3)
C6—C7—H7	120.5	C7'—C6'—N1'	121.2 (3)
C8—C7—H7	120.5	C11'—C6'—N1'	118.7 (3)
C9—C8—C7	121.4 (4)	C8'—C7'—C6'	119.8 (3)
C9—C8—H8	119.3	C8'—C7'—H7'	120.1
C7—C8—H8	119.3	C6'—C7'—H7'	120.1
C8—C9—C10	119.0 (3)	C7'—C8'—C9'	120.6 (3)
C8—C9—H9	120.5	C7'—C8'—H8'	119.7
C10—C9—H9	120.5	C9'—C8'—H8'	119.7
C9—C10—C11	120.8 (4)	C10'—C9'—C8'	119.8 (4)
C9—C10—H10	119.6	C10'—C9'—H9'	120.1
C11—C10—H10	119.6	C8'—C9'—H9'	120.1
C6—C11—C10	119.2 (3)	C9'—C10'—C11'	120.7 (4)
C6—C11—H11	120.4	C9'—C10'—H10'	119.6
C10—C11—H11	120.4	C11'—C10'—H10'	119.6
F3''—C12—F1''	110.4 (15)	C10'—C11'—C6'	119.1 (3)
F3''—C12—F2''	106.8 (15)	C10'—C11'—H11'	120.5
F1''—C12—F2''	105.9 (17)	C6'—C11'—H11'	120.5
F3—C12—F1	107.1 (4)	F2'—C12'—F3'	106.7 (3)
F3—C12—F2	106.0 (4)	F2'—C12'—F1'	107.2 (3)
F1—C12—F2	105.5 (4)	F3'—C12'—F1'	105.9 (3)
F3''—C12—C3	107.1 (14)	F2'—C12'—C3'	112.6 (3)
F1''—C12—C3	109.2 (19)	F3'—C12'—C3'	112.7 (3)
F2''—C12—C3	117.4 (19)	F1'—C12'—C3'	111.3 (3)
F3—C12—C3	113.5 (4)	O13'—C13'—C4'	118.0 (3)
F1—C12—C3	113.1 (3)	O13'—C13'—C14'	119.2 (4)
F2—C12—C3	111.1 (3)	C4'—C13'—C14'	122.9 (4)
O13—C13—C4	117.9 (3)	C13'—C14'—H14D	109.5
O13—C13—C14	118.9 (3)	C13'—C14'—H14E	109.5
C4—C13—C14	123.1 (3)	H14D—C14'—H14E	109.5
C13—C14—H14A	109.5	C13'—C14'—H14F	109.5
C13—C14—H14B	109.5	H14D—C14'—H14F	109.5
H14A—C14—H14B	109.5	H14E—C14'—H14F	109.5
C5—N1—N2—C3	0.0 (3)	C3—C4—C13—O13	179.8 (4)
C6—N1—N2—C3	178.1 (3)	C5—C4—C13—C14	179.1 (3)
N1—N2—C3—C4	0.4 (4)	C3—C4—C13—C14	−0.8 (6)
N1—N2—C3—C12	−178.7 (3)	C5'—N1'—N2'—C3'	0.1 (3)
N2—C3—C4—C5	−0.6 (4)	C6'—N1'—N2'—C3'	−176.9 (3)
C12—C3—C4—C5	178.3 (4)	N1'—N2'—C3'—C4'	0.0 (4)
N2—C3—C4—C13	179.3 (4)	N1'—N2'—C3'—C12'	177.4 (3)
C12—C3—C4—C13	−1.9 (7)	N2'—C3'—C4'—C5'	0.0 (4)
N2—N1—C5—O5	178.9 (3)	C12'—C3'—C4'—C5'	−177.1 (3)
C6—N1—C5—O5	1.1 (5)	N2'—C3'—C4'—C13'	179.4 (4)
N2—N1—C5—C4	−0.4 (4)	C12'—C3'—C4'—C13'	2.3 (7)
C6—N1—C5—C4	−178.2 (3)	N2'—N1'—C5'—O5'	179.5 (3)
C3—C4—C5—O5	−178.6 (3)	C6'—N1'—C5'—O5'	−3.9 (5)
C13—C4—C5—O5	1.4 (5)	N2'—N1'—C5'—C4'	−0.1 (4)
C3—C4—C5—N1	0.6 (3)	C6'—N1'—C5'—C4'	176.5 (3)
C13—C4—C5—N1	−179.3 (3)	C3'—C4'—C5'—O5'	−179.5 (3)
C5—N1—C6—C11	167.1 (3)	C13'—C4'—C5'—O5'	0.9 (5)
N2—N1—C6—C11	−10.6 (4)	C3'—C4'—C5'—N1'	0.1 (4)
C5—N1—C6—C7	−13.6 (5)	C13'—C4'—C5'—N1'	−179.5 (3)
N2—N1—C6—C7	168.8 (3)	C5'—N1'—C6'—C7'	−16.1 (5)
C11—C6—C7—C8	−0.2 (5)	N2'—N1'—C6'—C7'	160.2 (3)
N1—C6—C7—C8	−179.6 (3)	C5'—N1'—C6'—C11'	165.3 (3)
C6—C7—C8—C9	0.9 (6)	N2'—N1'—C6'—C11'	−18.4 (4)
C7—C8—C9—C10	−1.0 (6)	C11'—C6'—C7'—C8'	0.8 (5)
C8—C9—C10—C11	0.5 (6)	N1'—C6'—C7'—C8'	−177.7 (3)
C7—C6—C11—C10	−0.3 (5)	C6'—C7'—C8'—C9'	0.1 (6)
N1—C6—C11—C10	179.0 (3)	C7'—C8'—C9'—C10'	−0.8 (6)
C9—C10—C11—C6	0.2 (5)	C8'—C9'—C10'—C11'	0.6 (6)
N2—C3—C12—F3''	−59 (3)	C9'—C10'—C11'—C6'	0.4 (6)
C4—C3—C12—F3''	122 (3)	C7'—C6'—C11'—C10'	−1.1 (5)
N2—C3—C12—F1''	60 (3)	N1'—C6'—C11'—C10'	177.5 (3)
C4—C3—C12—F1''	−119 (3)	N2'—C3'—C12'—F2'	−2.5 (5)
N2—C3—C12—F2''	−179 (3)	C4'—C3'—C12'—F2'	174.5 (4)
C4—C3—C12—F2''	2(3)	N2'—C3'—C12'—F3'	118.3 (4)
N2—C3—C12—F3	−122.2 (5)	C4'—C3'—C12'—F3'	−64.8 (5)
C4—C3—C12—F3	59.0 (6)	N2'—C3'—C12'—F1'	−122.9 (4)
N2—C3—C12—F1	0.0 (6)	C4'—C3'—C12'—F1'	54.0 (5)
C4—C3—C12—F1	−178.9 (4)	C5'—C4'—C13'—O13'	0.7 (5)
N2—C3—C12—F2	118.4 (4)	C3'—C4'—C13'—O13'	−178.6 (4)
C4—C3—C12—F2	−60.4 (6)	C5'—C4'—C13'—C14'	180.0 (4)
C5—C4—C13—O13	−0.3 (5)	C3'—C4'—C13'—C14'	0.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O13	1.18	1.60	2.548 (3)	132
O5'—H5'···O13'	1.07	1.65	2.560 (4)	139
C14—H14B···F1'i	0.96	2.55	3.394 (5)	146
C7—H7···O13ii	0.93	2.64	3.446 (4)	145
C7'—H7'···O13'iii	0.93	2.57	3.406 (4)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O13	1.18	1.60	2.548 (3)	132
O5′—H5′⋯O13′	1.07	1.65	2.560 (4)	139
C14—H14B⋯F1′i	0.96	2.55	3.394 (5)	146
C7—H7⋯O13ii	0.93	2.64	3.446 (4)	145
C7′—H7′⋯O13′iii	0.93	2.57	3.406 (4)	149

Symmetry codes: (i) ; (ii) ; (iii) .